Water → HCID 131724395, compound

HRID 2083903Notes

Reaction equation

HRID 2083903 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.C(N(CC)CC)C.Br[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 68320Ethyl 3-bromopropionateHCID 113442904-chloro-2-methoxythiophenol

Product 1

HCID 131724395HCID 131724395, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-2-methoxythiophenol (5.78 g, 33 mmol), triethylamine (5.0 mL, 36 mmol) and ethyl 3-bromopropanoate (4.6 mL, 36 mmol) were dissolved in ethyl acetate (50 mL) and refluxed for 2 h. Water was added and the liquid phases were separated. The aqueous phase was extracted two times with ethyl acetate. The combined organic fractions were washed with 1 M aq. HCl and then concentrated in vacuo. Purification by flash chromatography (SiO2; heptane: dichloromethane (1:1, 0:1)) afforded the sub-title compound as a yellow solid. Yield: 3.0 g (30%). Estimated purity: 75% (NMR).

Workup

  1. temperaturerefluxed for 2 h
  2. customthe liquid phases were separated
  3. extractionThe aqueous phase was extracted two times with ethyl acetate
  4. washThe combined organic fractions were washed with 1 M aq. HCl
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (SiO2; heptane: dichloromethane (1:1, 0:1))

Sources & evidence

ORD record
ord-2338641d4b504ae2829b13830bb73896
Source dataset
uspto-grants-2004_04
Patent number
US06716834B2

Reaction notes

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